Trying to determine possible interest from coworker

[WH40KFan]

Hi, so I'm trying to determine if a coworker has developed some kind of feelings for me.  Let me explain the situation, I try to refrain from turning this into a wall of text that goes on for five thousand words. 

So I've been working remotely with three people for the past year and a half on a long term project.  We all three are remote and live in different states and initially we were meeting four hours a day going through various work issues.  That later turned into two hours a day.  The woman in question, let me call her Sara, is a project manager and the other person on the team is one of my direct reports, lets call him Dan.  I've worked with him for many years and consider him a good friend and I'd love his take on this but I don't want to put him into an awkward situation.  

So as you can imagine, working for four and then later two hours a day you get to know someone really well.  We all three get along great, there has never been a temper flare up or a harsh word or anything like that.  And we have a lot of fun swapping stories.  So Sara is in her mid 50's but she seems younger, she uses laughter as a common communication tool and jokes a lot.  She also uses emoji's a lot to react to messages on teams (more on that later) and its usually a laughing emoji.  Dan is a bit more reserved on the calls and on teams but he can let loose and tell some good stories too. Overall we are all three very comfortable and have a great rapport and enjoy working with each other.  Oh me and Dan, if I had to make a comparison that help frame how our relationship dynamic is I'd say I'm Maverick and he is Goose.  And that fits on a lot of levels.   

So let me start at the event that first made me wonder if Sara had feelings or at least some kind of a crush on me. So our project is winding down and we decided toward the end of last year that since we were working fewer and fewer issues that we would scale our meetings back from two hours a day everyday to only one hour on Tues/Thurs.  Sara had (couched in humor) joked how that made her sad and I assumed at the time she meant only sad about losing the daily contact.  So on the last meeting of our full group was going to be around December 17th I think, after that I was going to start my Christmas break.  Also on that day, our two hour meeting was abbreviated because of a conflicting meeting at the latter half we all had to attend so we only met for an hour.  As we were closing toward the end of that hour we were chatting and sharing some of things we were going to do over the break and I shared some pictures of gingerbread houses I had put together with my daughters and she dropped a heart emoji on them.  Now, let me say this, I have never up to this point seen her drop a heart emoji on anything.  She's just not that squishy emotive type.  She is high EI and armored but approachable.  So I didn't think anything of it really.  However about five minutes before the end of the meeting she stopped the work discussion cold and said basically "Drake, I want to stop right here before our next meeting and I want to personally wish you a wonderful time off and have a good time working on your model" (I'm a model kit guy and I had told Dan and Sara how excited I was to be building this over the holidays).  So that kinda was a "woah" moment.  But even more interesting was the sadness in her voice.  It was subtle and I honestly think I only recognized it from having gotten to know her over hundreds of hours.  It was sadness all the same and seemed vulnerable in that moment.  At the time I didn't think anything of it but later when I had time to process it I started wondering if something more was going on.  That was very unexpected.  Also, I noticed that later that week after Sara started her holiday she sent a message to Dan saying "I don't think we need to meet anymore this week, have a good holiday!".  He got a generic send off.  

So after that happened I started reviewing my interactions with her over the past year and a half in a different light.  Here's a synopsis of what I feel might have been key events:

--I actually confided in her about my teams security at this company shortly after I started working her.  She felt very trustworthy and this project we were on was coming from another project that had a lot of issues.  I told her I was concerned about my teams standing and she was very caring and let me know that anything said to her was said in confidence and that she had not heard that impression at all.  Yes there were issues but the overwhelming vibe she had gotten was how Sr. leadership was thrilled with this project despite its issues. 

--We only rarely turned our cameras on during teams meetings but I turned mine on once and she said "OMG you look just like my brother in law with that hat on!"  And she had to find the picture and show it to Dan and I.  And she continued with how her brother in law had some political ideas that he was very energetic about and she said he was lucky he was so hot otherwise no-one would talk to him.  I think it was more of his personality being off-putting than his specific beliefs.  But I filed that under "okay, so maybe she thinks I'm good looking"

--Dan and I are big nerds and I made an obscure Star Trek reference to something one time and she picked it up instantly.  She's not a nerd but she had seen this movie and she was so excited when I said that she said "oh! Oh! That was was from Wrath of Khan!"  I mean I couldn't see her face but I could tell she was smiling when she said it.  I told her great job, and that we'd make a nerd out of her yet.  

--One time Dan was out and I noticed she kept our full length 2 hour meeting for the next two days.  She and I did do some work and it went really well but we also spent a lot of time talking personal stuff.  She went down the road some of her political beliefs and after she explained a few things I told her "wow, it sounds to me like you are a 'thinking independent'".  She seemed to like that a lot.  I didn't judge her I just listened.  I was a bit shocked that she shared that much but I appreciated it and realized at the time that was unusual.  

--She is a joking person, uses a lot of "speaking while laughing" I guess is the way I'd call it.  She would also drop some innuendo sometimes.  It wasn't racy but it was there and that took me back a bit.  And she would do it on the 3 way call with Dan.  Again she would couch it with humor but some of the stuff she said was...interesting.  

--I'm the youngest of us three on the call.  One time the subject of our ages came up and I joked that I was ten years younger than I was (I used to do that with another coworker of mine and he usually fell for it so its an old gag I pull out every once in a while).  I'm actually 45 but I said on the call I was 35 and she said "wait, wait wait, you are 35?  That's my SON's age!"  And she said it with a bit of shock/disgust.  At the time I noted it but didn't think much of it.  In hindsight I wonder if she as potentially fantasizing about me a bit?  I don't know

--I've got a really good memory, I can recall conversations pretty well and she always seemed fascinated by that.  More than once I bring up some obscure thing she said and she would just say "omg, you remember everything, how do you do that?".  I think she liked the fact that I would listen to her. 

--We chatted (in the 3 way chat) in Teams and she sent a message to Dan and I about 30 minutes before midnight saying she was watching the ball drop in New Orleans.  I thought that was telling.  This was after the "big event" I go into below.  I messaged her in the one-on-one teams channel with her about a few interesting places to go in New Orleans (I live in Louisiana), she didn't message me back.  When we got back in the office at the beginning of January she told me she was watching the ball drop in New Orleans on TV and she said "Oh if I was that close to you (New Orleans) I would defiately reach out to you and see if we could meet, absolutely"

There are other examples but that's some of the ones that took place prior the sad goodbye (with the exception of the New Orleans one).  

So the next thing that happened I kind of brought it on and escalated it myself.  I was about two days into my Christmas break and she and I had continued to chat on teams a bit even though I was off.  So I'm a night owl and I was staying up late one night trying to make sure that a short-term disability claim came though for one of my employees.  I wanted to make doubly sure all of that processed for them on time.  Now, I tend to unwind on these breaks with a few beers so I was a bit intoxicated.  Also it was about 3 in the morning.  As I was checking emails I saw an email come through from a person that the three of us have had some challenging work discussion with.  So I fired up teams and sent a message to her and ranted about this person in humorously drunk fashion that I think she would find entertaining.  But in hindsight my message to her wasn't so much about the rant, I think I wanted her to know in a round-about way that I picked up on her sad good bye.  Well it must have worked because she replied back very warmly and in her humorous way.  I opened up a bit on what I was doing that night and I did it in a way that I haven't quite done before.  She ultimately replied with a lightly flirty message with some mild innuendo.  I replied back in my own cheeky way and I matched her innuendo and she dropped a heart emoji on my reply.  From the woman who never drops heart emojis.  

So I feel like that was the...pivotal moment I guess.  There's a lot more that but again I'm trying to keep this short.  She's continued to engage with me in chat, even for nonsense and I say the engagement in the one-on-on teams chat has actually increased since we got back from Christmas.  We've recently has this ice storm in the south and I was out of power for a few days and Dan had to be out for a few days due to family issues and just this week Sara was out for a few days dealing with some surgery for her mom.  She commented on Monday "Me you and Dan might need to go back to 2 hour meetings so we can catch up on everything!"  

So finally, she had to be out part of this week for her Mom's surgery.  She setup 30 minutes to talk with me about a work realted issue and when I joined that call she was very happy.  She confessed to me "I'll tell you I almost cancelled this meeting becasue I've had back to back meetings and I haven't eaten lunch yet but I really wanted to jump on the call and catch up and gossip"  And we did, she started into work stuff but then she veered off on her mom's condition.  I felt bad and I asked her "Do you have a meeting after this one?  I feel bad, don't chat with me if you are hungry, don't let me hold you up"  She said it was no big deal, she actually grabbed some healthy chicken nuggets while we were chatting and she felt better.  I took that to mean she really didn't want to get off that call with me.  And even though she had another meeting after hours she was 5 minute late for that one because we kept chatting.  

And finally, I forwarded an email to her on Friday that I think that is a work related good-to-know but I was mainly using it as a pretense to send her something to see if she would reply.  And she did, she replied very warmly on Saturday, her day off.  

Again, there is more I could go into but since the drunk message and her flirty reply things seem to be slowly but steadily going up, at least that's my read.  So what's the verdict, is it likely she into me in more than a platonic sense?  Do I need to clarify anything?  

Thank you for reading this wall of text. 

[flitzanu]

12 hours ago, WH40KFan said:

Hi, so I'm trying to determine if a coworker has developed some kind of feelings for me.  Let me explain the situation, I try to refrain from turning this into a wall of text that goes on for five thousand words. 

 

Thank you for reading this wall of text. 

ask them out, you'll have your answer.

[FredEire]

It seems like you are trying to crack some kind of da Vinci code here based on every interaction you've had.

You can't do it. Most of the time these things come down to gut feeling, and you might be wrong. If your gut feeling is she likes you, ask her to coffee/a dinner and if she says no well hey you took your shot!

[FredEire]

It seems like you are trying to crack some kind of da Vinci code here based on every interaction you've had.

You can't do it. Most of the time these things come down to gut feeling, and you might be wrong. If your gut feeling is she likes you, ask her to coffee/a dinner and if she says no well hey you took your shot!